Association of 6-oxo-piperidine-2-carboxylic acid with penicillin V. Production on Penicillium chrysogenum fermentations.
Analysis of a 13C NMR spectrum of a concentrated broth from Penicillium chrysogenum fermentation revealed the presence of penicillin V and 6-oxo-piperidine-2-carboxylic acid(1) as the principal constituents. The latter lactam, identical to an authentic sample prepared by the cyclization of alpha-aminoadipic acid was present to the extent of 28 mol% of penicillin V. The lactam isolated form the broth was nearly racemic, having a slight excess of the L-isomer. This isolation provides further evidence regarding the biosynthetic precursors of the hydrophobic penicillins.
D002250:Carbon Radioisotopes; D003470:Culture Media / Q000032:analysis; D005285:Fermentation; D007769:Lactams / Q000032:analysis / Q000096:biosynthesis* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D010404:Penicillin V / Q000032:analysis / Q000096:biosynthesis* / Q000302:isolation & purification; D010407:Penicillium / Q000378:metabolism*; D010408:Penicillium chrysogenum / Q000378:metabolism*; D010875:Pipecolic Acids
C030878:6-oxopiperidine-2-carboxylic acid; D002250:Carbon Radioisotopes; D003470:Culture Media; D007769:Lactams; D010875:Pipecolic Acids; D010404:Penicillin V